Be Careful What You Hope For

I grew up as a normal American boy.... Air Force brat, moved around a lot... finally settled in Atlanta. I played sports, liked and pursued girls, got into and out of trouble. Every once in a while though, I went through some gay sex fantasy phases. I'd think about it, masturbate to thoughts of it, and even played with my asshole while jerking off on occasion. But these phases would be short lived... a few days here and there throughout the year, all while I'd be in relationships with girlfriends and such. This went on through jr. and sr. high school, and through my two years in college. After college, I hung out in Atlanta for a few more years. And, the fantasies continued.

One of my favorite things was to look at the local independent news paper- Creative Loafing. It had personal ads in the back for people to hook up. I'd read through them every week and have fantasies about the one that stuck out the most.... Ironically, it was about the ads of men claiming that their cock stuck out the most! As a young man in my early twenties, I always seemed to enjoy the thought of being with older men... older, well-endowed men. See, I'm not packin' a huge cock. It's about 5 ½ inches and average thickness. Ever since I saw my first porno, I envied the large penis. So, in my mind, I gravitated toward what I didn't have.... BIG cock. By this time, I'd already invested in a couple dongs and dildos for play. I'd cram them up my ass and fuck myself real good while jerking off. It was great, but I couldn't help but wonder what it would be like to be fucked by a man... someone else controlling the fucking.... Not my hands doing it.

After a rather nasty break up with a girl,... OK, I got seriously dumped... heart broken and all, I didn't want much to do with chick for a little while. I resumed my gay fantasies after a pretty long hiatus. I grab and paper and glanced over the ads. Boy, did one sick out.

SWM- 50 yrs old- WELL hung- seeking younger newbie to show the ropes- N. GA Mountains- BOB.

It also listed his phone number- this was before the internet had come on full swing. So, after a couple nights of thinking about it, I decided to pick up the phone and call the number. I was so nervous. I didn't know what to say. He answered the phone and I weakly spoke:

"Is this Bob?

He replied, "uh, yes it is. Can I help you?"

I said, "Hi. I'm calling about your ad in the paper, the personal ad?"

I could tell that he knew I was nervous. He was very calm and patient with me. He assured me that I had nothing to be nervous about because nothing would happen that I didn't want to happen, in that conversation or beyond. He asked me why I was calling and I told him about my fantasies mainly involving thoughts of older men that were well hung. How I was primarily straight but was in between relationships and figured it might be a good time to act on some fantasy. I told him that his ad seemed sincere and that's what I needed.... He assured me that he would be nothing but kind, gentle, and patient with me. So, after a few more short phone conversations, I finally asked what I could expect in an encounter with him considering that I knew nothing about gay sex. Bob, then told me how me might introduce me. He said, "Well, I'd love for you to come up to my cabin here in the mountains. We could have a drink and chat, but I usually like to just get down to the fun. I'd like to initially just please you, and not ask much of you. Obviously if you wanted to do things to me, I'd be open to that, but most of the first- timers that I've been with have been so over-whelmed that it's better for me to lead. I'd probably start by undressing you, and rubbing my hands over your body. I'd be pretty quick to get my mouth on your cock. I'd certainly love to eat out your ass and then if you were up for it, I'd love to fuck you."

"Wow" I said. "You make it sound so easy, and laid back. When can we meet?"

He said, "What are you doing tonight?"

I couldn't think of anything. I was off work the next day. I really had no reason to not do it other that fear.... And I wasn't going to let fear get in my way. So I told him that I'd come up there. He sounded thrilled with himself that he had not scared me off and that me was gonna possibly get some action that night. He told me that his cabin was a little off the beaten path and that he meet me at a gas station in a nearby town and let me follow him to his cabin. We planned on meeting at 8:00. I spent the rest of the day just dreaming about what the night might hold. I showered and was very careful to clean myself very thoroughly. I dressed fairly casual not thinking that we'd be out in public or anything. I grabbed a couple condoms from my drawer just incase he didn't have any, and just incase it actually went as far as him fucking me. When it was time, I hopped in my truck and headed up to the mountains.

The whole way up, about a 80 minute drive, I was so nervous.... half way talking myself out of doing it, and then, remembering how long I'd been waiting to do something like this. I finally reached the town where I was to meet Bob and started looking for the gas station. As I approached it, I had one last mental freak out before telling myself, "You got this, and you're gonna love it!"

I parked my truck and waited. With each approaching pair of headlights, I wondered if this was the one. Finally, Bob arrived, pulling up right next to me and smiling in a very understanding kind of way. He knew that this was a big step for me. He said, "Follow me. Once we get to my driveway, you can get into my truck and I'll drive us up to my cabin. It's really steep and with it being dark, it would be hard for anyone to manage the drive up." I nodded and off we went. It was about a 10 minute drive of a nerves roller coaster. After I got past the thoughts of "is this guy an axe murderer?", I couldn't help but wonder how big his cock really was. He described it as large and pleasing but didn't get into specifics. His break lights snapped me from my train of thought and we slowed down to his property. I took a deep breath, grabbed my back pack which had a change of clothes, and some toiletries and such in it, and got out of my car. I locked up and hopped in with Bob. It really was dark out there and I had no idea how he managed to get up that hill so quickly, all while rubbing my leg and then my crotch. I didn't even know that I was hard until his hand touch me. He said that he was glad to see that I was excited about being there.

Once we got up to his place, we got out of the car and it seemed like in no time at all we were climbing up his stairs inside to his bedroom. I needed to use the restroom after the drive, and did but then it was his show. He was ready. He knew that I had never been with a man and was excited to get first crack at me. He slowly walked over to me and hugged me. He tried to kiss me but I shied away. I didn't really want to kiss... for me, that's for the ladies.

He slowly removed my shirt and began rubbing my body. He licked my nipples and they were hard in an instant. I was shaking with nerves and excitement. He grabbed my belt buckle and unfastened it to free my shorts. As they dropped to the floor, he followed them. He tugged at my boxer shorts and my cock popped out to be greeted with a grin. I was shy about my smallish cock but he said, "this is perfect for sucking." And then in one foul swoop, he took it in his mouth to the base... It was right then that I knew that I was in for a treat.